Showing metabocard for Surfactin (MMDBc0018590)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 08:46:20 UTC
Update Date2025-10-07 16:04:16 UTC
Metabolite IDMMDBc0018590
Metabolite Identification
Common NameSurfactin
DescriptionSurfactin is a lipopeptide belonging to the chemical class of biosurfactants. It is produced by various Bacillus species, particularly Bacillus subtilis, and is characterized by its unique cyclic structure composed of a fatty acid chain linked to a peptide ring. The chemical structure of surfactin includes a β-hydroxy fatty acid and a cyclic heptapeptide, which contributes to its surface-active properties. Surfactin is involved in several biochemical pathways, including antifungal activity, as evidenced by the identification of biosynthetic genes such as srfAB in the genomes of Bacillus species (PMID:41050548 ). It has been shown to inhibit biofilm formation in various bacterial strains, with a minimum biofilm inhibitory concentration (MBIC) of 5 µg/mL, significantly reducing extracellular polymeric substances on surfaces (PMID:41011461 ). Additionally, surfactin, along with other lipopeptides, plays a role in the biosynthesis of antifungal compounds, as confirmed by genome sequencing studies (PMID:41050548 ). The presence of surfactin in Bacillus-HT1 and Bacillus-HT2 highlights its potential as an eco-friendly antimicrobial agent (PMID:41031829 ). Overall, surfactin's unique chemical properties and its involvement in various biosynthetic pathways underscore its significance in microbial ecology and potential applications in biocontrol.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fc976dd1200>


  Mrv1652305152110462D          

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M  END
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3D MOL for #<Metabolite:0x00007fc976dd1200>

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3D SDF for #<Metabolite:0x00007fc976dd1200>

  Mrv1652305152110462D          

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    6.3911    1.2363    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    0.6578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5706    1.1168    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 23 22  1  0  0  0  0
 30  2  1  0  0  0  0
 30  3  1  0  0  0  0
 30 24  1  0  0  0  0
 31  4  1  0  0  0  0
 31  5  1  0  0  0  0
 31 25  1  0  0  0  0
 32  6  1  0  0  0  0
 32  7  1  0  0  0  0
 32 26  1  0  0  0  0
 33  8  1  0  0  0  0
 33  9  1  0  0  0  0
 33 27  1  0  0  0  0
 34 10  1  0  0  0  0
 34 11  1  0  0  0  0
 35 21  1  0  0  0  0
 35 28  1  0  0  0  0
 36 22  1  6  0  0  0
 37 24  1  6  0  0  0
 38 25  1  6  0  0  0
 39 26  1  6  0  0  0
 40 29  1  6  0  0  0
 41 27  1  6  0  0  0
 42 28  1  0  0  0  0
 43 23  1  0  0  0  0
 44 29  1  0  0  0  0
 45 34  1  1  0  0  0
 46 36  1  0  0  0  0
 47 37  1  0  0  0  0
 48 38  1  0  0  0  0
 49 40  1  0  0  0  0
 50 39  1  0  0  0  0
 51 45  1  0  0  0  0
 52 41  1  0  0  0  0
 53 36  1  0  0  0  0
 53 42  2  0  0  0  0
 54 37  1  0  0  0  0
 54 46  2  0  0  0  0
 55 38  1  0  0  0  0
 55 49  2  0  0  0  0
 56 39  1  0  0  0  0
 56 47  2  0  0  0  0
 57 40  1  0  0  0  0
 57 51  2  0  0  0  0
 58 41  1  0  0  0  0
 58 48  2  0  0  0  0
 59 45  1  0  0  0  0
 59 50  2  0  0  0  0
 42 60  1  4  0  0  0
 61 43  2  0  0  0  0
 62 43  1  0  0  0  0
 63 44  2  0  0  0  0
 64 44  1  0  0  0  0
 46 65  1  4  0  0  0
 47 66  1  4  0  0  0
 48 67  1  4  0  0  0
 49 68  1  4  0  0  0
 50 69  1  4  0  0  0
 51 70  1  4  0  0  0
 71 52  2  0  0  0  0
 72 35  1  0  0  0  0
 72 52  1  0  0  0  0
 73 35  1  0  0  0  0
 36 74  1  6  0  0  0
 37 75  1  6  0  0  0
 38 76  1  1  0  0  0
 39 77  1  1  0  0  0
 40 78  1  6  0  0  0
 41 79  1  6  0  0  0
 45 80  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0018590

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C1(CCCCCCCCCCC)CC(O)=N[C@@]([H])(CCC(O)=O)C(O)=N[C@@]([H])(CC(C)C)C(O)=N[C@]([H])(CC(C)C)C(O)=N[C@@]([H])(C(C)C)C(O)=N[C@@]([H])(CC(O)=O)C(O)=N[C@]([H])(CC(C)C)C(O)=N[C@@]([H])(CC(C)C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C52H91N7O13/c1-12-13-14-15-16-17-18-19-20-21-35-28-42(60)53-36(22-23-43(61)62)46(65)54-37(24-30(2)3)47(66)56-39(26-32(6)7)50(69)59-45(34(10)11)51(70)57-40(29-44(63)64)49(68)55-38(25-31(4)5)48(67)58-41(27-33(8)9)52(71)72-35/h30-41,45H,12-29H2,1-11H3,(H,53,60)(H,54,65)(H,55,68)(H,56,66)(H,57,70)(H,58,67)(H,59,69)(H,61,62)(H,63,64)/t35?,36-,37-,38+,39+,40-,41-,45-/m0/s1

> <INCHI_KEY>
AFWTZXXDGQBIKW-DZESRJJCSA-N

> <FORMULA>
C52H91N7O13

> <MOLECULAR_WEIGHT>
1022.336

> <EXACT_MASS>
1021.667486018

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
163

> <JCHEM_AVERAGE_POLARIZABILITY>
113.49782090616043

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3S,6R,9S,12S,15R,18S,21S)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-12-(propan-2-yl)-25-undecyl-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
11.691674644666666

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.3144193667065034

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9050872278486506

> <JCHEM_POLAR_SURFACE_AREA>
329.03

> <JCHEM_REFRACTIVITY>
271.15440000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.99e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3S,6R,9S,12S,15R,18S,21S)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-25-undecyl-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for #<Metabolite:0x00007fc976dd1200>
Download
PDB for #<Metabolite:0x00007fc976dd1200>
HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0     -13.404   0.230   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.803   5.223   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.813   7.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.128  -1.687   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.118  -4.156   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.316   9.354   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.950   7.245   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.060  -1.464   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.050  -3.933   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.583   5.137   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.216   3.028   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.070   1.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.737   0.230   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.403   1.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.069   0.230   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.736   1.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.402   0.230   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.068   1.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.735   0.230   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.401   1.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.067   0.230   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.411   5.810   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.999   6.424   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.446   5.583   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.485  -2.047   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.307   6.886   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.417  -1.824   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.091   1.995   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.346  -0.744   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.021   6.166   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.911  -2.630   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.524   7.828   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.842  -2.407   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.791   3.611   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.266   1.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.586   4.280   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.654   4.057   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.277  -0.521   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.514   5.360   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.138   0.782   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.209  -0.298   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.674   3.421   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.824   7.954   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      13.771  -1.327   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      14.573   2.668   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.011   3.697   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       8.872   5.000   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.852   0.062   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      10.920  -0.161   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      12.940   4.777   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      14.781   1.142   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.991  -1.241   0.000  0.00  0.00           C+0
HETATM   53  N   UNK     0       2.210   3.307   0.000  0.00  0.00           N+0
HETATM   54  N   UNK     0       6.229   4.640   0.000  0.00  0.00           N+0
HETATM   55  N   UNK     0       9.495   0.422   0.000  0.00  0.00           N+0
HETATM   56  N   UNK     0      10.297   4.417   0.000  0.00  0.00           N+0
HETATM   57  N   UNK     0      13.563   0.199   0.000  0.00  0.00           N+0
HETATM   58  N   UNK     0       5.634  -0.881   0.000  0.00  0.00           N+0
HETATM   59  N   UNK     0      13.148   3.251   0.000  0.00  0.00           N+0
HETATM   60  O   UNK     0      -0.137   4.730   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       3.062   8.870   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       0.412   8.567   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      14.989  -0.384   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      13.979  -2.853   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       5.219   2.171   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0       8.664   6.526   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0       6.644   1.588   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      11.985  -1.273   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0      14.157   5.720   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0      16.206   0.559   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0       3.199  -2.767   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0       1.566  -0.658   0.000  0.00  0.00           O+0
HETATM   73  H   UNK     0       2.600   1.770   0.000  0.00  0.00           H+0
HETATM   74  H   UNK     0       3.760   2.750   0.000  0.00  0.00           H+0
HETATM   75  H   UNK     0       7.862   2.531   0.000  0.00  0.00           H+0
HETATM   76  H   UNK     0       9.703  -1.104   0.000  0.00  0.00           H+0
HETATM   77  H   UNK     0      12.732   6.303   0.000  0.00  0.00           H+0
HETATM   78  H   UNK     0      11.930   2.308   0.000  0.00  0.00           H+0
HETATM   79  H   UNK     0       4.001   1.228   0.000  0.00  0.00           H+0
HETATM   80  H   UNK     0      15.998   2.085   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   30                                                            
CONECT    3   30                                                            
CONECT    4   31                                                            
CONECT    5   31                                                            
CONECT    6   32                                                            
CONECT    7   32                                                            
CONECT    8   33                                                            
CONECT    9   33                                                            
CONECT   10   34                                                            
CONECT   11   34                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   35                                                       
CONECT   22   23   36                                                       
CONECT   23   22   43                                                       
CONECT   24   30   37                                                       
CONECT   25   31   38                                                       
CONECT   26   32   39                                                       
CONECT   27   33   41                                                       
CONECT   28   35   42                                                       
CONECT   29   40   44                                                       
CONECT   30    2    3   24                                                  
CONECT   31    4    5   25                                                  
CONECT   32    6    7   26                                                  
CONECT   33    8    9   27                                                  
CONECT   34   10   11   45                                                  
CONECT   35   21   28   72   73                                             
CONECT   36   22   46   53   74                                             
CONECT   37   24   47   54   75                                             
CONECT   38   25   48   55   76                                             
CONECT   39   26   50   56   77                                             
CONECT   40   29   49   57   78                                             
CONECT   41   27   52   58   79                                             
CONECT   42   28   53   60                                                  
CONECT   43   23   61   62                                                  
CONECT   44   29   63   64                                                  
CONECT   45   34   51   59   80                                             
CONECT   46   36   54   65                                                  
CONECT   47   37   56   66                                                  
CONECT   48   38   58   67                                                  
CONECT   49   40   55   68                                                  
CONECT   50   39   59   69                                                  
CONECT   51   45   57   70                                                  
CONECT   52   41   71   72                                                  
CONECT   53   36   42                                                       
CONECT   54   37   46                                                       
CONECT   55   38   49                                                       
CONECT   56   39   47                                                       
CONECT   57   40   51                                                       
CONECT   58   41   48                                                       
CONECT   59   45   50                                                       
CONECT   60   42                                                            
CONECT   61   43                                                            
CONECT   62   43                                                            
CONECT   63   44                                                            
CONECT   64   44                                                            
CONECT   65   46                                                            
CONECT   66   47                                                            
CONECT   67   48                                                            
CONECT   68   49                                                            
CONECT   69   50                                                            
CONECT   70   51                                                            
CONECT   71   52                                                            
CONECT   72   35   52                                                       
CONECT   73   35                                                            
CONECT   74   36                                                            
CONECT   75   37                                                            
CONECT   76   38                                                            
CONECT   77   39                                                            
CONECT   78   40                                                            
CONECT   79   41                                                            
CONECT   80   45                                                            
MASTER        0    0    0    0    0    0    0    0   80    0  160    0
END

Download
3D PDB for #<Metabolite:0x00007fc976dd1200>
Download
SMILES for #<Metabolite:0x00007fc976dd1200>
[H]C1(CCCCCCCCCCC)CC(O)=N[C@@]([H])(CCC(O)=O)C(O)=N[C@@]([H])(CC(C)C)C(O)=N[C@]([H])(CC(C)C)C(O)=N[C@@]([H])(C(C)C)C(O)=N[C@@]([H])(CC(O)=O)C(O)=N[C@]([H])(CC(C)C)C(O)=N[C@@]([H])(CC(C)C)C(=O)O1
Download
INCHI for #<Metabolite:0x00007fc976dd1200>
InChI=1S/C52H91N7O13/c1-12-13-14-15-16-17-18-19-20-21-35-28-42(60)53-36(22-23-43(61)62)46(65)54-37(24-30(2)3)47(66)56-39(26-32(6)7)50(69)59-45(34(10)11)51(70)57-40(29-44(63)64)49(68)55-38(25-31(4)5)48(67)58-41(27-33(8)9)52(71)72-35/h30-41,45H,12-29H2,1-11H3,(H,53,60)(H,54,65)(H,55,68)(H,56,66)(H,57,70)(H,58,67)(H,59,69)(H,61,62)(H,63,64)/t35?,36-,37-,38+,39+,40-,41-,45-/m0/s1
Download
Synonyms
ValueSource
3-[(3S,6R,9S,12S,15R,18S,21S)-9-(Carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-12-(propan-2-yl)-25-undecyl-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoateGenerator
Molecular FormulaC52H91N7O13
Average Mass1022.336
Monoisotopic Mass1021.667486018
IUPAC Name3-[(3S,6R,9S,12S,15R,18S,21S)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-12-(propan-2-yl)-25-undecyl-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid
Traditional Name3-[(3S,6R,9S,12S,15R,18S,21S)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-25-undecyl-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid
CAS Registry NumberNot Available
SMILES
[H]C1(CCCCCCCCCCC)CC(O)=N[C@@]([H])(CCC(O)=O)C(O)=N[C@@]([H])(CC(C)C)C(O)=N[C@]([H])(CC(C)C)C(O)=N[C@@]([H])(C(C)C)C(O)=N[C@@]([H])(CC(O)=O)C(O)=N[C@]([H])(CC(C)C)C(O)=N[C@@]([H])(CC(C)C)C(=O)O1
InChI Identifier
InChI=1S/C52H91N7O13/c1-12-13-14-15-16-17-18-19-20-21-35-28-42(60)53-36(22-23-43(61)62)46(65)54-37(24-30(2)3)47(66)56-39(26-32(6)7)50(69)59-45(34(10)11)51(70)57-40(29-44(63)64)49(68)55-38(25-31(4)5)48(67)58-41(27-33(8)9)52(71)72-35/h30-41,45H,12-29H2,1-11H3,(H,53,60)(H,54,65)(H,55,68)(H,56,66)(H,57,70)(H,58,67)(H,59,69)(H,61,62)(H,63,64)/t35?,36-,37-,38+,39+,40-,41-,45-/m0/s1
InChI KeyAFWTZXXDGQBIKW-DZESRJJCSA-N